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The Boston Celtics may not have reached the 2020 NBA Finals, but they have a credible claim to the title of "best team in the Eastern Conference." They outscored the Miami Heat in an Eastern finals series that they lost in six games, the first two of which were played without Gordon Hayward. Their second-round series followed a similar trajectory. Despite Hayward's absence, they actually outplayed the Toronto Raptors somewhat easily, winning the series by 38 points but needing seven games to seal the deal. Their regular-season resume doesn't hold a candle to the Milwaukee Bucks', but remember, their five best players missed 70 combined games. We barely saw Boston's completed roster, and it still almost reached the Finals. 

There are weaknesses to be addressed, but the reasons the Celtics lost aren't necessarily fixable through offseason moves. It really boiled down to bad luck late in games. They outscored regular-season opponents by 4.4 points per 100 possessions in clutch situations, and then got outscored by 23.7 points per 100 by the Raptors and Heat. Nothing they do this offseason could prevent, say, OG Anunoby's miraculous Game 3 buzzer-beater. Clutch numbers, even in the playoffs, tend to be somewhat random outside of a few isolated superstars. Jayson Tatum projects as an ideal late-game closer. He's going to get better with another postseason under his belt. 

The Celtics don't have to go all-in yet. All evidence suggests that they're already close to a championship-caliber team, and neither of their two best players have seen their 25th birthday yet. That should lead to a wider scope for the Celtics this offseason. Their moves aren't necessarily going to be based purely on winning right now. They can focus on the three-to-five-year window that they almost certainly have. Expect younger targets and financial prudence as we preview Boston's 2020 offseason. 

One note before beginning: We will be using Spotrac for player salaries, and 2019-20 cap numbers for this exercise as a whole. That includes previously agreed-upon numbers like the rookie scale and the minimum salary. A frozen cap is the likeliest outcome of negotiations between the league and the NBPA, but these numbers could theoretically change in either direction. 

Under the assumption that the 2019-20 numbers will be used, these are the pertinent numbers for these projections. 

Salary cap

$109,140,000  

Luxury tax  

$132,627,000  

Luxury tax apron  

$138,928,000  

Salary floor  

$98,226,000  

Non-taxpayer mid-level exception (Year 1)  

$9,258,000  

Taxpayer mid-level exception (Year 1)  

$5,718,000  

Cap room mid-level exception (Year 1)  

$4,767,000  

Bi-annual exception  

$3,623,000

Cap situation and overall finances

Boston may or may not have a championship roster yet, but it is certainly paying for one. The Celtics are a staggering $17 million above the 2019-20 luxury tax line at this moment. Before a single move is made, these obligations would create a $36 million tax payment in addition to their total salary. 

Players

2020-21 Salary

Kemba Walker

$34,379,100

Gordon Hayward*

$34,187,085

Jaylen Brown

$23,883,929

Marcus Smart

$13,446,428

Jayson Tatum

$9,897,120

Enes Kanter*

$5,005,350

Daniel Theis**

$5,000,000

Romeo Langford

$3,631,200

Vincent Poirier

$2,619,207

Grant Williams

$2,498,760

Robert Williams

$2,029,920

Semi Ojeleye**

$1,752,950

Carsen Edwards

$1,517,981

Javonte Green**

$1,517,981

Guerschon Yabusele (dead salary)

$1,039,080

Demetrius Jackson (dead salary)

$92,857

No. 14 pick

$3,458,400

No. 26 pick

$2,035,800

No. 30 pick

$1,936,440

Total

$149,929,588

*player option
**non-guaranteed

The Celtics' financial commitments are so great that they literally can't fit all of them on the roster. They currently have 17 players and first-round picks for 15 slots. That doesn't even include restricted free agent Brad Wanamaker, who may simply lose a game of musical chairs here (especially if the Celtics want to give his minutes to their younger guards). They have moves to make, and expect them to be aggressive. Boston is heavily incentivized to avoid the tax this season. 

Jaylen Brown's second contract kicks in next season. Jayson Tatum's is coming, and may cost 30 percent of the cap, thanks to the Rose Rule, which states that a team is not allowed to have two designated players on their roster at the same time. Kemba Walker is making the max for the next three years. Oh, and Marcus Smart is only two seasons away from a new contract of his own. The Celtics are going to be expensive for the foreseeable future. The dreaded repeater tax triggers after three consecutive tax seasons, or when a team pays it four years out of five. The Celtics might be willing to pay up eventually, but no ownership group is going to pay it forever. Savings now could keep Boston's window open a year longer down the road. 

There are smaller moves that could help save some money. Vincent Poirier is almost certainly getting dumped in a trade. He isn't playing for this team next season. Enes Kanter is more expensive, but fits the same mold. They will almost certainly trade away some or all of their draft picks. But those are supplementary moves. Their tax status is going to come down to Gordon Hayward and that enormous $34.2 million player option. 

Do the Celtics want him back? Maybe. Hayward is still a valuable player when healthy, and he's an insurance policy against a prolonged absence from Tatum or Brown. There are theoretical financial benefits to him opting in. His contract is expiring, so Boston could resolve to keep him, take another run at the title, and then let him walk just as its roster hits its most expensive point. A trade, on the other hand, likely brings in long-term money. A potential path to repeater tax avoision might involve paying it next season, and then ducking below the line for the 2021-22 season. That at least buys Boston time. 

What can't be denied is this: If Hayward opts into that $34.2 million figure and remains in Boston, the Celtics are paying the tax. They would probably prefer not to do that, so it's worth discussing the four possible ways they could avoid that. 

  • Hayward opts out based on a pre-arranged extension. He would have to cut his 2020-21 salary in half to get the Celtics below the tax. That's a four-year pact at around $76 million. He isn't taking that, but there's a framework here. Say Hayward demands $100 million over four years. That's a first-year salary hovering around $22 million, putting them a couple of cap dumps away from the tax line. The downside, of course, is that it means committing three extra expensive years to Hayward. 
  • Hayward opts out and leaves for nothing. Boston goes from deep in tax territory to far enough below the line to use the full mid-level exception comfortably. The argument here is, essentially, that Hayward is better than anyone they could sign with that exception, but not so much better that he warrants a tax bill for that meager gap. This is a weak market, and that exception could get Boston a strong player. Danilo Gallinari wants to sign with a winner. Would you rather have Gallinari for $9.3 million, or Hayward for $34.2 million? This is the least likely scenario. Hayward shouldn't turn down $34.2 million in a depressed market given his injury history, but it can't be ruled out. 
  • Hayward opts out and cooperates on a sign-and-trade. This makes Hayward available to most of the NBA, with the only exceptions being the contenders unable to hard-cap themselves by acquiring a player through sign-and-trade (think Golden State and Philadelphia). The fact that Hayward could negotiate a new salary with the acquiring team removes the primary financial obstacle, as they would be able to find a number that both facilitates a trade and makes sense on their books for the long haul. 
  • Hayward opts in, and Boston trades him wherever it wants. This would keep Hayward's larger cap figure intact, but open the entire NBA up as possible trade partners, as a Hayward acquisition in this manner wouldn't trigger a hard cap. All it would take would be around $27.4 million in matching salary. That's easier for some teams than others. Not everyone can afford a $34.2 million acquisition. Those that can, however, wouldn't have to make a long-term commitment to Hayward. 

None of this rules out a possible return to Boston, but the Celtics have real reason to move on from Hayward, at least at his current cap figure. There are pros and cons to each of these methods, and we'll discuss them in a bit more depth later on. For now, let's pivot into Boston's (surprisingly barren) cupboard of draft picks, and how that might inform the Hayward situation. 

Draft capital

  • 2020 picks: Nos. 14, 26, 30, 47
  • Owed future first-round picks: N/A
  • Incoming future first-round picks: N/A

Remember when Boston had a seemingly endless war chest of future draft picks to dangle in trades? Well, that's gone now. If the 2020 NBA Draft passes without a deal, the Celtics would not own a single draft pick from another team for the first time in nearly a decade. This should be categorized as extremely unlikely. The Celtics have 14 players and four draft picks. They couldn't keep everyone even if they wanted to. There are going to be trades. 

In a perfect world, Boston would probably prefer not to use any of these picks. Who are the Celtics going to draft, even at No. 14, that would definitely play for them next season? This has been a common theme for Boston over the past decade:  It has so many draft picks that each subsequent pick becomes less valuable because there just aren't any available minutes to develop them with. The Celtics already have Romeo Langford, Robert Williams, Grant Williams and Carsen Edwards in the pipeline. The last thing they need is more developmental talent. 

If the Celtics do use a pick, the goal should be to take a foreign prospect that they don't need to bring over yet. If they resolve to trade all of them, there are three logical goals: 

  • Dump salary: This should be relatively simple. Cap space teams are usually open to taking on bad money in exchange for draft capital. The Knicks stand out as an easy example here. They have more cap space than they could possibly use, but as the Marcus Morris trade proved, they value late first-round picks. The Knicks would probably take on Kanter and Poirer to get their hands on No. 26 and No. 47. Atlanta, who took on Allen Crabbe from Brooklyn last offseason, is another option in this vein. 
  • Acquire a future pick: The longer the Celtics can wait to avoid making a pick, the better. That gives them more flexibility in trade talks, and prevents them from taking a player they won't use. The No. 14 pick obviously has the most value. This draft isn't top-heavy, but the consensus is that good players will be available through the first round. All they'd need is one team to fall in love with a particular prospect and boom, the Celtics have a trade partner. 
  • Include a pick in a Hayward deal as a sweetener: Many of the players Boston might target with Hayward are more valuable than he is. They might need to sweeten the pot a bit, and their own future picks are expected to be so low that they aren't particularly valuable. 

If Boston does wind up keeping its picks, there isn't an easy need to identify. Yes, it could use improvement at center and backup point guard, but it already have prospects there. The Celtics don't have any young, up-and-coming wings on the bench, but they have two future stars there. That makes this simple: If they keep any of their picks and take players it expects to roster next season, they'll just lean on the best available prospect. Hopefully it doesn't come to that. There will almost certainly be a place for some of their picks in Hayward talks, at the very least. 

Trade options

Boston's trade outlook is almost entirely based on Hayward. Tatum and Brown aren't going anywhere. The city might revolt if Smart got dealt, and Walker's contract would limit the return beyond a worthwhile point. Any major Celtics trade would have to be built around Hayward, and there are two routes the Celtics could take here. The obvious is to try to use Hayward to upgrade their biggest weakness: center. Bam Adebayo killed the Celtics in the Eastern Conference finals, but dealing Hayward for a big man could offer Boston an antidote to the NBA's best bigs. Four established names stand out. 

  • Myles Turner is the name you're going to hear most often, both in Boston talks and rumors involving other teams, and rightfully so. Indiana has two expensive centers and seems to prefer the idea of only keeping one. Turner's shooting and rim protection makes him a fit almost anywhere, but especially in Boston. Think back on Brad Stevens' big men. Al Horford, Aron Baynes and Daniel Theis can all shoot. He prizes five-out spacing, and Turner could provide it. Reports have suggested that the Pacers are interested in Hayward, an Indiana native. Boston would probably have to include another asset. That likely wouldn't bother Danny Ainge. Money is a concern as well. The small-market Pacers aren't coming close to the tax, so this would either need to be a cheaper sign-and-trade or a bigger deal involving multiple players. Turner makes around half as much as Hayward, but the injured Jeremy Lamb stands out as salary the Pacers probably wouldn't mind dumping. Turner, based on his age and shooting, is probably Boston's preferred target. 
  • Steven Adams is probably available, and what he lacks in shooting, he makes up for as a rebounder. The Thunder might take Hayward as salary filler, but wouldn't view him as a positive rebuilding asset. This is, realistically, a three-team trade involving another team that values him more. The Celtics would ship Hayward to a team that would, in turn, pay Oklahoma City for Adams before shipping him off to Boston. The salaries are closer here, with Adams making $27.5 million. 
  • Nobody knows if Rudy Gobert is on the block, but sooner or later, the Jazz are going to have to make a decision on the supermax contract he is already eligible for. Gobert will be 29 before that contract kicks in and 34 when it ends. If they want to take a step back and find younger assets to pair with Donovan Mitchell, Gobert is their logical trade piece. Boston would probably be at the back of the line to start given its lack of high-upside assets, but if a better deal doesn't materialize, something around Hayward along with a combination of the Celtics' young players and picks could get a deal done. The irony of Hayward returning to Utah in a deal shipping out Gobert would be delicious. 
  • One more center name to watch: Jarrett Allen. There isn't a way to make the money work with Hayward, but maybe as part of a three- or four-team deal, or even as a swap involving some of Boston's 2020 picks. The Nets seem deadset on DeAndre Jordan as their starting center. The Celtics would love a clear starting-caliber big man on a rookie deal. So would most teams.

The alternative route is to trade Hayward with the understanding that such a deal would make the Celtics worse next season. In exchange, they could save money and pick up some future assets. 

  • Miami has an interesting set of expiring deals in Andre Iguodala and Kelly Olynyk (another shooting big man Stevens knows well), and the Heat pitched Hayward in 2017 free agency. A rules quirk makes it tough for the Heat to access their future draft picks for trades, but it's doable if necessary. The real question is how motivated Boston would be to help the Heat right now. 
  • Portland could use a wing upgrade, has expiring salary to trade and could offer some interesting young players (Zach Collins, Gary Trent Jr., Anfernee Simons, Nassir Little). 
  • By internet law, we have to mention the Knicks in any trade talks involving a declining star. They'd prefer to sign him outright after an opt out, but if he opts in, the Celtics could try to extract some draft capital to move him into New York's cap space. That would also create a hefty trade exception. 
  • Sticking to the desperate big-market motif, Otto Porter Jr.'s expiring contract and some draft picks make sense if the Bulls want to win right now. 

There are plenty of other options. Hayward fits on almost any team, and if the Celtics want to move him, they shouldn't find it particularly difficult to do so. 

What would an ideal offseason look like?

There are three scenarios on the table: one in which Hayward opts in and stays, one in which he is traded and one in which he leaves outright. An extension is possible, but given Boston's long-term financial outlook, it is probably the least likely. 

  • If Hayward stays, the plan is probably to offload salary and commit to letting him go in 2021 in order to avoid paying that season's tax. This plan is straightforward. The Celtics would bring back the bulk of its 2019-20 team and hope that better health and luck along with some moves on the fringes would be enough to put them over the top. Kanter and Poirer are the easiest dumps. If the Celtics are willing to go deeper into the tax for a one-year free agent at the taxpayer mid-level exception, some of the older centers would probably be targeted. Dwight Howard might take that sort of offer. Boston would love to have Baynes back, but he should expect to get more. Paul Pierce openly pitched Tristan Thompson on joining the Celtics via buyout at the trade deadline. Maybe he'd consider a one-year offer if his market is dry? Ownership would probably prefer to avoid using the exception, though, and instead focus on developing the two incumbent young centers. 
  • If Hayward leaves for nothing, go throw the full MLE at the best available player. The Celtics can be flexible positionally. If they sign a center, Smart gets a promotion into Hayward's starting slot. If it's another wing, turn around and offer the bi-annual exception to a cheaper center as an additional option there, and continue to bring Smart off the bench. Gallinari would be the best mid-level target under this scenario. He fits so cleanly into Hayward's role for a far lower price, and as well as Boston shot as a team last season, it lacked a single deadeye target. Gallinari fixes that. If the Celtics believe they have minutes for rookies in this situation, they also have the money to use their picks. A defensive-minded wing to complement Gallinari off the bench would be ideal at No. 14, and this draft has plenty. 
  • If a Hayward trade comes, it almost has to be for a center. Turner should be the first choice, and if Stevens can get him to increase his 3-point volume meaningfully (a safe bet considering the Pacers were almost always at the bottom of the league under Nate McMillan), he might actually be a steal on his current contract. This should be viewed as Boston's best-case scenario overall. If the Celtics can swap Hayward for Turner, that could fill their biggest short- and long-term hole with a 24-year-old and potentially avoid the tax as an added bonus. 

Door No. 1 is probably the likeliest. Door No. 2 creates the most optionality. Door No. 3 is the best-case scenario. The ball is in Hayward's court now, but no matter what he does, the Celtics can rest easy knowing that they're already comfortably in the championship conversation.